


Down We Go

by SailoLee



Series: Kinktober 2018 [1]
Category: Teen Wolf (TV)
Genre: Anal Fingering, Begging, Deepthroating, Edgeplay, Face-Fucking, Kinktober 2018, M/M, Praise Kink
Language: English
Status: Completed
Published: 2018-10-09
Updated: 2018-10-09
Packaged: 2019-07-28 14:43:51
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,744
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16243790
Author URL: https://archiveofourown.org/users/SailoLee/pseuds/SailoLee
Summary: Stiles had the thought a few times. But he never meant to blurt it out to Derek in a hotel room.





	Down We Go

**Author's Note:**

> I am participating in Kinktober this year! My first month long challenge thing. So this was originally on supposed to be day 1. Buuuuuut when I sat down and started typing it out it ran away and now it's covering three days (deep throating, begging, edgeplay) So we'll see how the others go. I'm a little behind but I'll catch up.
> 
> Fair warning Derek is kind of OOC, Idk how it happened. But I don't think it's too bad.

The first time Stiles meets Derek his initial thought (behind the raw, primal fear) was that this guy was _massive._ The second was just a quick whisper in the back of his racing mind that he was likely proportional everywhere else as well. It was swept away in the wave of fear and adrenaline he was experiencing. It didn’t come back for quite some time.

~~~

The second time it comes to his mind is when they’re floating in the pool, Stiles having to hold up a mostly paralyzed Derek away from a pacing Kanima and why was this his life now? Right. Werewolf best friend, cool. He’s anchoring Derek with one arm crossed over Derek’s chest and he can’t help but notice that, despite his rather lengthy arm span, he barely crosses the expanse of Derek’s chest. On one hand he has the opportunity to feel Derek up just a bit with a legitimate excuse without threat of having his throat ripped out by werewolf teeth. On the other, Derek’s size makes it very hard to keep both of them afloat and Stiles has to seriously doggy paddle one armed just to keep them from drowning until the Kanima leaves or help comes. So there they are, desperately trying to not drown and his stupid lizard (ha ha) brain starts to think about how firm Derek’s muscles are and how he really does just dwarf Stiles. And if he dwarfs him _everywhere._ The thought flies away again as the Kanima renews its efforts to get to them. It isn’t until later, after they’ve escaped the Kanima and Derek is decidedly unparalyzed that Stiles has a moment to analyze his recent thoughts of Derek.

Stiles had never felt an attraction to men. To be honest the only people he’d ever had any sort of romantic feelings towards were Lydia and his childhood friend Heather, however fleeting that may have been. With Derek though, how could you not be attracted to the guy? And since Stiles was never really one to restrict himself on pretty much anything, this sudden attraction didn’t exactly unnerved him. It’s not like Derek would ever know, right?

~~~

Stiles had always had an oral fixation, that wasn’t a secret. It was something he was often made fun of for by assholes like Jackson, stupid comments in middle and high school about always shoving something into his mouth. So it was no surprise to Stiles himself that he really wanted to try oral sex with a guy. He had come out to himself and his friends and family not long ago, around the end of his senior year of high school as bisexual, pansexual, somewhere along those lines. So it also wouldn’t be shocking or embarrassing for him to be seen with another guy. It was a totally natural thing.

Blurting out, “I want to suck your dick!” To Derek out of nowhere in their shared hotel room was probably the worst way to go about it though.

They were on their way back to beacon Hills after Stiles had painstakingly tracked down Derek to help him save Scott’s ass once more and they had stopped for the night in a low budget highway hotel. The room was small, two beds and a bathroom with a TV that probably had been bought in the 80’s but it was clean and comfortable enough for a one night stay. They hadn’t talked much after the first hour of Derek getting in his jeep Roscoe, Stiles giving him a crash course in everything that had happened since he’d left Beacon Hills. They had let the radio do the talking, Stiles solely focused on the journey ahead in a strangely solemn seeming to Derek. In reality Stiles had just been thinking about how derek looked really good, probably better than before he’d left which, that’s incredibly unfair you ass, and he was trying very hard to hide it. And now, thanks to the filter that had been covering his brain to mouth for the first half of their time together very suddenly and inexplicably disintegrating, Derek was now standing in front of Stiles with a gaping mouth in shock.

Derek stood in front of his bed, pants unbuttoned to remove them for bed and that’s when Stiles had lost all self control apparently. “What?” And Stiles could feel the blush rising steadily up his neck over his face, but he almost burst out laughing at the truly dumbfounded look on Derek’s face. It was just so uncommon a look for the older man that Stiles was almost sure he was dreaming. Almost wished it as well. “N-Nothing, just ignore-!”

“Okay.”

Now it was Stiles turn to gape in disbelief as Derek continued unbuttoning his pants, pushing them down his thighs partway. “I-I-Seriously? You’re not fucking with me are you?” Derek glared at Stiles, eyebrows furrowed in that familiar way that caused quite a bit of nostalgia to come over Stiles for a moment. “You offered, so why not. I don’t mind if you don’t. We’re alone and as long as you stay quiet no one has to know.” Stiles blinked in disbelief as Derek grunted in frustration. “Are you going to do it or not?” It was like teleportation to Stiles. One second he’s sitting on the edge of the other bed, the next he’s on his knees in front of Derek, eagerly helping to push down the jeans trapping the object of his desire. Stiles felt himself shiver as he came face to face with Derek’s boxers and a decidedly large outline. Derek shuffled a bit, kicking off the jeans fully before looking down at Stiles with an arched eyebrow. Tentatively Stiles reached a hand up and caressed the bump in front of him. His fingertips dipped under the edge of the boxers and he slowly, very very slowly, pulled them down until they were around Derek’s knees. Stiles waited for Derek to sit on the edge of the bed until he wrapped his hand around the length that had been a subject of his teenage fantasies for a few years now.

It was thick, surprisingly so was Stiles first thought. Derek was still mostly soft though with every slow pass of Stiles fist moving up and down with gentle pressure he started growing. And growing. And growing _jesus_ was it going to stop? With his hand still making soft stroking motions Stiles looked up at Derek with wide eyes. “I haven’t...I’ve never uh…” Derek just continued looking down at Stiles, a heat in his gaze that Stiles had never experienced with anyone in his life. “Just do what you think feels right. Just watch the teeth and you’ll be fine.” Derek growled and Stiles shifter as his own pants starting getting a bit uncomfortably tight. Stiles moved his gaze back to the cock in his hand but Derek placed a large hand on Stiles hair and he looked back up attentively. “Look at me when you do it.” Stiles breathing was picking up a bit and he nodded quickly.

Stiles leaned forward a bit and stuck his tongue out for his first, timid lick at the head, catching the taste. He groaned quietly and moved in more, popping the head into mouth faster than either of them were expecting and sealing his lips around it. Derek huffed a quick breath out of his nose and started scratching his short nails into Stiles scalp gently, encouragingly. Stiles blinked big doe eyes at Derek as he took a bit more in his mouth, going slow trying to test his as of yet unfound boundaries. He brought one hand to gently stroke what he couldn’t fit yet and the other was rubbing at Derek’s thigh, mouth still setting a steady rhythm. In, out, breath, more, in, out, more, breath. Over and over, never once waving in his eye contact with Derek. Then suddenly Derek gripped his hair in a firm but still rather gentle fist and started pushing a bit, hips moving. Derek leaned down so he was closer to Stiles asking, “Think you can take more?” His voice was deeper and huskier than normal and Stiles felt his hips jerk a bit as he nodded eagerly.

Derek started pushing Stiles down a bit more forcefully, not giving him as much of a chance to pull back, but Stiles didn’t complain. He was about halfway down now and already he was feeling the struggle to take the last bit. But if nothing else no one could ever say Stiles wasn’t determined. So he braced both hands on Derek’s thighs and surged forward quickly. “Jesus _Stiles!_ ” Derek’s lustful growling of his name was well worth the soreness he was definitely going to have tomorrow. Or in a few minutes because hot damn he got it all in. And without gagging though for some reason Stiles wasn’t too shocked by this since he’d never had much of a gag reflex for anything. There wasn’t enough room in Stiles mouth for anything except Derek’s dick and he was drooling quite an embarrassing amount but Derek didn’t seem to mind. His head was thrown back, eyes closed and his nails were scratching at Stiles scalp again. His decidedly much sharper nails since, Stiles now noticed, derek had slipped into Beta mode.

Stiles pulled back to take a deep breath before going back down to the root and _swallowing_ so that Derek thrust forward roughly. Suddenly Stiles felt a leg slip between his, startling him and Derek smirked down at him. “Need help?” He muttered and Stiles felt his foot pressing against his dick and Stiles couldn’t help but whimper, which Derek seemed to enjoy. “Come here.” One hand on his head and the other behind his neck Derek grabbed at Stiles and shoved, turning Stiles head slightly to the side where he wanted it. With small movements Derek started moving Stiles mouth up and down, completely controlling his movements for his own pressure, his foot rubbing at Stiles still covered crotch at the same time. Stiles was in heaven and his hips started humping Derek’s leg a bit, eyes shutting in bliss. “Eyes up!” Stiles snapped his eyes open and stared up at Derek, face flushed and Derek could clearly see the outline of his dick moving up and down Stiles’ throat.

What little control Derek had left went crashing down and with a snarl he jumped to his feet. Grabbing Stiles head between both his hands he started fucking Stiles’ face with earnest, Stiles hands skirting up his hips to his stomach, still grinding on Derek’s leg. “Come on baby, come on there we go, so good for me, so good, Jesus Stiles so good for me baby.” Derek was muttering little epithets to the human at his feet. “God I’m gonna cum, Stiles.” Derek started pulling back but Stiles grabbed at the back of Derek’s thighs and held himself still, swallowing continuously. “Ugh Stiles, wait!” It was too late however and Derek roared as he came down Stiles throat, the boy swallowing as fast as he could to keep down the flood of warm cum. When it started tapering off Stiles began pulling off, suckling gently to catch every drop. He finally pulled off with a little ‘ _pop_ gasping softly. He licked up and down the length, laving his balls as well, taking each into mouth individually before working his way back up to the head. He kept up gentle suction, drawing out Derek’s orgasm until the older man gently moved him off and sat down heavily on the bed again.

Derek’s eyes were full of wonder as Stiles rested his head on Derek’s knee, breathing deeply. Then he realised something. Stiles was definitely still very much hard. “Stiles.” the boy’s head snapped up, attention completely devoted to Derek, his mouth all swollen and pink from where Derek had fucked him perhaps a bit too hard. “Stand up.” Stiles blinked but did as told and stood in front of Derek. Keeping eye contact with him all the while, Derek leaned forward and kissed Stiles stomach gently while unbuttoning his jeans. He pulled down his pants and boxers at the same time, Stiles stumbling out of them clumsily. Derek grabbed at the edge where Stiles thigh met his ass and manhandled him into his lap, one leg on each side of Derek’s hips. Stiles whipped off his shirt as well and Derek smiled at him, wrapping his hand around Stiles’ erection in a loose fist. “You want to come baby?” Derek whispered and Stiles nodded whimpering as his thrusts were met with Derek pulling his hand away a bit. A hot tongue laved at one of his nipples, his free hand going to Stiles ass and massaging with rough pressure. “Derek. Oh shit, Derek please.” Stiles whined and Derek chuckled, taking the nipple in his mouth biting down gently. “You can do better than that Stiles. Come on, beg me to cum.”

Stiles sobbed a bit, overwhelmed but loving it. “Derek please, please oh God let me cum please, please.” Stiles buried his face into Derek’s neck, continuing his pleas as Derek was still barely touching him. Stiles heard Derek moving and the hand on his ass left for a moment before two fingers returned slightly wet. Stiles keened, high and loud as Derek started circling his hole gently, pushing a bit before retreating and repeating the circular motion. “Have you ever fingered yourself?” derek asked and Stiles nodded fervently, still hiding his face in Derek’s shoulder, hot tears pouring onto Derek’s shoulder as he whispered, “A-a little.” Teeth nibbled at his ear and Stiles Back arched as Derek slowly, gently pushed a finger in. His hand wrapped a little firmer around Stiles and the boy was _gone_ babbling incoherently, little pleas for more, to come please pleasepleasepleaseeplease. But Derek was insistently slow, dragging his finger in and out at a snail’s pace, his equally as slow, palming at the head before stroking down the side once.

Derek finally added his second finger and Stile gave a guttural moan, hands curling up to weave into Derek’s hair. “Ride my fingers baby, come on.” Stiles needed no further instruction and threw himself back onto the thick fingers, nearly dislodging himself from Derek’s lap. “Easy, easy I’ve got you.” Derek peppered little kisses across Stiles freckled shoulders, tonguing a path between each one in a nonsensical pattern as Stiles started riding his hand at a gentler pace. He brought one hand to clutch at Derek’s shoulder, the other still in his hair and leaned back to look in Derek’s face. “God you look so amazing baby. Look at you taking my fingers so good, do you like that? Like my fingers in you, my hand on you?” Stiles just rode a bit faster, finding his grip in Derek’s lap to go harder. “Need to cum baby? Ready to cum?” Derek asked, lips brushing against Stiles’ stomach. “Yes, yes please can I cum Derek please? Please let me cum!” Stiles begged between his tears and Derek beamed with pride. “Ok baby you can cum.” And with that Derek started fingering Stiles in earnest, his hand suddenly flying on Stiles cock.

Stiles squealed and went boneless, Derek still moving as his hips jerked slightly. “There there there there there Derek Derek Derek DEREK!” With one last scream of Derek’s name Stiles went rigid and his mouth hung open soundlessly as he came all over Derek’s hand and some on his stomach. Derek grunted, feeling Stiles body clench down on his fingers, doing his best to work Stiles through the orgasm as he had for him. When Stiles started shifting his hips away rather than towards Derek stopped and muttered a litany of praise on the boy, laying him down gently. Stiles’ face was completely fucked out, eyes distant and dazed, a bit of drool coming from the corner of his mouth. “Holy fuck Derek. Shit.” Stiles wheezed as Derek laid next to him. Gentle claw tipped fingers ran up and down his chest while Stiles recovered. “We gotta do that more often.” Derek chuckled a bit and leaned into Stiles face. “We have plenty of time after we save Scott’s ass from whatever paranormal bullshit he has going on now. I wouldn’t want this to be a one-off.” Stiles hummed in affirmative and rolled onto his side to cuddle contently. “Definitely doing this again.”

**Author's Note:**

> This is the filthiest thing I have ever written oh my god.


End file.
